Thank you to everyone who tuned in live today!
In this livestream conversation, I sat down with Substack writer and podcaster Jonathan Small to talk about what it really means to navigate work, identity, reinvention, and retirement as members of Generation X.
Jon and I traveled different career paths. He moved from magazine publishing to digital media, podcasting, and entrepreneurship. Check out his current Substack publication, Small Talk.
I shifted from a big-tech career (e.g., Apple, IBM, eBay, Yahoo) into independent coaching as a solopreneur. But we’ve both lived through the same constant pattern: industries rise, industries fall, and Gen X is constantly forced to reinvent itself.
We talked about how traditional career expectations failed our generation. The idea of a stable, decades-long job with a pension evaporated. Entire fields collapsed (e.g., print magazines, early tech companies), and many people clung to the past too long, only to find themselves shut out of the future.
What has kept the survivors afloat is adaptability. As I shared in the conversation, I’ve learned to watch the “canaries in the coal mine” and pivot before a company or industry fails. Jon had to make similar leaps as the print media industry imploded around him.
A big theme was identity. Many Gen X professionals still define themselves by job titles, employers, or industries that may no longer exist. Jon and I both experienced that moment of losing our “main character” identity and having to figure out who we were without our familiar career spotlight. It’s painful at first, but eventually liberating. Your profession is not your identity! The sooner you separate the two, the stronger and more resilient you become.
We also talked about the realities of ageism, unstable 401(k)s, and the pressure of being the “sandwich generation,” caring for both aging parents and kids heading to college. It’s no wonder so many Gen Xers feel anxious about retirement. But despite all of this, our generation remains remarkably resilient. Someone in the chat joked that we’re the “Chumbawamba generation”—we get knocked down, we get back up again. And it’s true.
One of the most important takeaways from our conversation is the shift toward multiple income streams. Many of us no longer expect one job to provide all of our income, meaning, or stability. Check out Free Agent Nation by Daniel Pink.
Jon and I both shared how life improved once we stopped forcing a single revenue source to carry everything.
More flexibility.
More time with family.
More control of our energy.
More meaningful work, on our own terms.
We also touched on the growing loneliness many mid-career adults face, especially when office culture disappears. Building community (e.g., through platforms like Substack and online groups) and collaborating have become essential. Sharing your work publicly, even imperfectly, helps replace that lost connection. And as I emphasized, the antidote to fear isn’t perfection. It’s showing up consistently.
We ended on a hopeful note. As Gen Xers, we’re entering what Jon called Chapter Three of our lives. It’s the stage where experience, autonomy, creativity, and wisdom finally converge (think Yoda).
We don’t need to chase the identity we had at 25. We get to design something new. The internet gives everyone the opportunity to build their own platform, reach people globally, and create a working life that fits who they are now.
Would you like to talk with me about planning the next phase of your career? You can always schedule a complimentary call.
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I’m Larry Cornett, an executive coach who works with ambitious professionals to help them reclaim their power, become more invincible, and create better opportunities for their work and lives. Do more of what you love and less of what you hate! 📕 Check out The Invincible Daily Journals!
